This paper describes the Application Information Mapping Test (AIMT) a type of content-level test procedure for Business-to-Business (B2B) integration across enterprises. The goal of AIMT is to assure that the semantics of a B2B message element are interpreted by the system under test (SUT) according to the element s intended meaning. AIMT provides this assurance by verifying that the element values are correctly processed, stored, and utilized by the SUT to reflect that intended meaning. This paper discusses the AIMT methodology for test development and test execution, which is based on our experience to provide a self-testing capability in a B2B-interoperability project for automotive industry. In particular, we propose an efficient and robust test procedure for AIMT which reduces the time-consuming manual steps and prevents mapping errors. This procedure also proposes a minimum set of test trials by considering practical message constraints of industrial environments. A simulation experiment is presented and results are analysed with respect to the effectiveness of the approach.